Here Is How You Juggle Multiple Bosses Without Going Nuts

Good communication and time management are key to keeping your sanity while working with more than one boss.

Image courtesy of Pixabay

Managing her four bosses had been Alice’s daily battle for nearly two years, and to add insult to injury, they all lacked empathy and organization skills. They would flood her calendar with tasks she had to work at least ten hours a day to meet extremely tight deadlines — without cutting corners of course. The perfect recipe for anxiety and burnout.

Let me first brief you on Alice’s four wonder-bosses. They were big on gossip, encouraged bad behavior across the firm, provoked envy among team members, they were skilled at undermining their best talents, did not appreciate hard work, believed they were not obliged to pay people in exchange for their services and, above all, they were not aligned. One of them was inherently insecure, deceitful and manipulative. So you know what kind of madness she had to deal with and the two main challenges she faced every day: having to please several bosses, and working in a toxic work environment.

As quoted by a Harvard Business Review article, Robert Sutton, a professor of management science and engineering at Stanford University and the author of “Good Boss, Bad Boss”, said, “It is extremely common these days to have more than one boss. As you to go to a matrixed structure, you can easily have between one and seven immediate supervisors.”

1) Resort to the Eisenhower Decision Matrix for better time management.

Your workload must be overwhelmingly high, and time is quite a critical factor in every project, so you need to first organize your priorities before helping others get organized. Draw a matrix with four to-do lists:

  1. Urgent and important.
  2. Not urgent but important.
  3. Urgent but not important.
  4. Not urgent and not important.

Urgent tasks require your immediate attention while important ones are what contributes to your long-term missions and objectives.

Share your matrix with your bosses and make sure they help you decide what is most urgent and most important.

One of Alice’s bosses would send her the first task, say, now and write, “Please, this is so urgent, I need it in 30 minutes!” When getting the task beautifully done actually required at least an hour, and in around ten minutes, she’d send her another task and say, “Please, I need this in an hour!”. Alice knew she couldn’t hand both around the same time, so she assumed her boss might had forgotten her first ‘urgent’ task and she emailed her saying, “You have sent me task ABC ten minutes ago, so which one of these two is more urgent? I cannot finish both within the time frame you’ve provided. Please advise.” And bossy boss would advise… only she still thought Alice could work miracles all the time.

2) Guide your bosses’ communication process.

If your bosses were showering you with tasks, it is very likely that you will end up with overlapping deadlines. The main reason behind this is lack of cross-departmental alignment and poor internal communication. They don’t know who’s sending you what and what you already have on your plate. We are all busy, and when we have this one go-to employee who will do the job right and on time, we feel more than happy to dump all the important tasks on him/her.

Effective internal communication can do wonders: it ensures coordination, largely contributes to job satisfaction, results in mutual trust, decreases turnover rates, facilitates decision-making and boosts productivity through leaving employees motivated, informed, educated and inspired. Many small firms are not aware of the importance of internal communication and believe tasks alone are what should receive their undivided attention.

Be proactive and do the following:

  1. Plan a weekly meeting (or web conference) for all your bosses. They need to communicate and understand the workload and challenges you’re facing.
  2. Get them to actually speak to one another — face to face or through the phone, coordinate with one another and decide who needs your immediate attention most. When two deadlines overlap, ask Boss#1 to give a call to Boss#2 in order to coordinate (but don’t do so unless you’ve informed both parties — will explain why in the next point). That leaves you out of the drama.
  3. Use an online platform for organizing projects like Basecamp, Asana or Projecturf, and make sure all your bosses can view your projects.
  4. Create time blocks in your calendar and share it with all bosses so they’d know what time is reserved for what — and whose — task.

3) Manage the communication between your bosses.

Practically, you are the boss, or else why do you think several bosses had to share your services? Communication is your magic tool, so make sure it flows continuously and smoothly in all directions.

Nevertheless, bringing your bosses together isn’t enough. You, too, need to communicate effectively and proactively with them, in addition to managing the communication between them.

Remember the insecure boss I mentioned in the second paragraph? Let’s name him Scar — like the villain from Disney’s Lion King, and we’re naming the other boss Ursula. One day, Ursula sent Alice a very important, time-critical task, and on that same day, Scar asked her to finish something which was not urgent. Given her experience with Scar, Alice asked Ursula to coordinate with him.

Within an hour, Scar stomped over to Alice in a fit of fury and said in a very hostile tone, “How exactly was I interrupting your work with Ursula?”

The first thing that occurred to Alice was: What in hell did she say to him? Because she was close to the bottom of the food chain, Scar most likely assumed he could chew her out and not Ursula indeed.

Defensively, Alice looked Scar in the eyes and sternly said, “I did not say you were interrupting my work with Ursula. It must have been miscommunicated to you.”

His expression and tone immediately morphed from a blood-thirsty vampire’s to that of someone with severe diarrhea. “I was just asking what other tasks you had.” He said, turning the poor-ole-me act on.

“Your tone suggested otherwise.” Alice replied — she was very stressed and putting up with his insecurities wasn’t on her to-do list.

Scar marched away from Alice then stopped, turned to face her and said at the top of his lungs, “I am the Executive Manager and you will follow my orders.”

I honestly don’t remember ever joining the army! Alice thought then said, “Discuss this with Ursula; you two are holding senior roles… practice some communication.”

The two managers were terrible communicators, but since Alice’s goal is to finish her projects very smoothly, it would have been best if she had first spoken to Scar and informed him that Ursula would give him a call to further explain what project she’d assigned to her. That way, she wouldn’t have created unnecessary and unwelcome conflict with someone who was not there to add value but to sabotage anyone who did.

4) Speak up.

Advocate for yourself and speak your piece. When things go out of hand, or when you feel overworked, make sure you communicate this very clearly to your supervisor.

Learn to say “no” when necessary and call it a day when you’re fed up. No one said you had to work overtime… especially when you’re not getting paid for it. We are mere mortals, and thus we need our beauty sleep or else we won’t be of any help to anyone — not even ourselves.

Alice was burning the candle at both ends each and every day. At the end, she got exhausted and burned-out, and she was underpaid and underappreciated. You may be passionate about what you do, but you are no superwoman or superman, so take good care of your health and mental well-being. If your managers cannot understand or accept this, then you should definitely start job hunting.

5) Take it easy.

You were not hired to please everyone. Your job is to work a certain number of hours every day with a few breaks, deliver high-quality services and improve the business. If things go wrong, that’s okay. You did your job, you tried hard but things didn’t go as planned. That’s okay; it’s a part of doing business.

Don’t stress over the things you can’t control. Seek the advice of mentors and professionals, and, above all, be good to yourself. Treat yourself with love, courtesy and empathy.